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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:12 UTC

Update Date

2023-02-21 17:20:18 UTC

HMDB ID

HMDB0031301

Secondary Accession Numbers

HMDB31301

Metabolite Identification

Common Name

2-Octen-4-one

Description

2-Octen-4-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. 2-Octen-4-one is a fruit, jam preserves, and metallic tasting compound. 2-Octen-4-one has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and nuts. This could make 2-octen-4-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Octen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2E)-2-Octen-4-one	HMDB
Butyl propenyl ketone	HMDB
FEMA 3603	HMDB
Propenyl butyl ketone	HMDB

Chemical Formula

C₈H₁₄O

Average Molecular Weight

126.1962

Monoisotopic Molecular Weight

126.10446507

IUPAC Name

(2Z)-oct-2-en-4-one

Traditional Name

(2Z)-oct-2-en-4-one

CAS Registry Number

4643-27-0

SMILES

CCCCC(=O)\C=C/C

InChI Identifier

InChI=1S/C8H14O/c1-3-5-7-8(9)6-4-2/h4,6H,3,5,7H2,1-2H3/b6-4-

InChI Key

FMDLEUPBHMCPQV-XQRVVYSFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0031301)
Cell membrane (HMDB: HMDB0031301)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031301)

Source

Endogenous

Endogenous (HMDB: HMDB0031301)

Plant

Plant (HMDB: HMDB0031301)
Poaceae (HMDB: HMDB0031301)

Exogenous

Food

Food (HMDB: HMDB0031301)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Nut

Nuts (FooDB: FOOD00869)

Exogenous (HMDB: HMDB0031301)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031301)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	179.00 to 180.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1045 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.157 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.56 g/L	ALOGPS
logP	2.57	ALOGPS
logP	2.84	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	40.34 m³·mol⁻¹	ChemAxon
Polarizability	15.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	132.818	30932474
DeepCCS	[M-H]-	130.304	30932474
DeepCCS	[M-2H]-	167.154	30932474
DeepCCS	[M+Na]+	141.895	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	127.3	32859911
AllCCS	[M+NH4]+	135.5	32859911
AllCCS	[M+Na]+	136.7	32859911
AllCCS	[M-H]-	134.1	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	139.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.51 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2432 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1908.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	475.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	312.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	545.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	585.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1233.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	413.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1215.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	445.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Octen-4-one	CCCCC(=O)\C=C/C	1333.5	Standard polar	33892256
2-Octen-4-one	CCCCC(=O)\C=C/C	990.1	Standard non polar	33892256
2-Octen-4-one	CCCCC(=O)\C=C/C	1006.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Octen-4-one,1TMS,isomer #1	C/C=C\C(=CCCC)O[Si](C)(C)C	1229.0	Semi standard non polar	33892256
2-Octen-4-one,1TMS,isomer #1	C/C=C\C(=CCCC)O[Si](C)(C)C	1191.4	Standard non polar	33892256
2-Octen-4-one,1TBDMS,isomer #1	C/C=C\C(=CCCC)O[Si](C)(C)C(C)(C)C	1453.9	Semi standard non polar	33892256
2-Octen-4-one,1TBDMS,isomer #1	C/C=C\C(=CCCC)O[Si](C)(C)C(C)(C)C	1379.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Octen-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-9000000000-0a51643f674832ad7d21	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Octen-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Octen-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 10V, Positive-QTOF	splash10-004i-0900000000-cf57086d78d3c23f95bb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 20V, Positive-QTOF	splash10-056u-9400000000-2efd8909de766eb1846c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 40V, Positive-QTOF	splash10-052f-9000000000-0e00b0e75db928dabab7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 10V, Negative-QTOF	splash10-004i-1900000000-2d8ac5b499bd5711c413	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 20V, Negative-QTOF	splash10-004i-7900000000-4461568451fe240fa278	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 40V, Negative-QTOF	splash10-00lu-9000000000-6f147016e6474082d122	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 10V, Negative-QTOF	splash10-004i-0900000000-76b7c4a7bc4810b17f31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 20V, Negative-QTOF	splash10-017i-9300000000-653670661b093f4f4e91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 40V, Negative-QTOF	splash10-0159-9000000000-a17063f7688822d3bd0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 10V, Positive-QTOF	splash10-0a4j-9000000000-2fdadca08c65d5c36f7e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 20V, Positive-QTOF	splash10-014i-9000000000-e1e855222dae0350c5fc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Octen-4-one 40V, Positive-QTOF	splash10-066u-9000000000-cdc94c2b99c7bdea886c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003353

KNApSAcK ID

Not Available

Chemspider ID

20122184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12409825

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Octen-4-one (HMDB0031301)

MOL for HMDB0031301 (2-Octen-4-one)

3D MOL for HMDB0031301 (2-Octen-4-one)

3D SDF for HMDB0031301 (2-Octen-4-one)

3D-SDF for HMDB0031301 (2-Octen-4-one)

PDB for HMDB0031301 (2-Octen-4-one)

3D PDB for HMDB0031301 (2-Octen-4-one)

SMILES for HMDB0031301 (2-Octen-4-one)

INCHI for HMDB0031301 (2-Octen-4-one)

Structure for HMDB0031301 (2-Octen-4-one)

3D Structure for HMDB0031301 (2-Octen-4-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra